25-((1S)-10-camphorsulfonyloxy)-27-isopropoxy-26,28-dihydroxycalix[4]arene | 1052211-45-6

• 分子结构分类: 有机化合物 - 脂质和类脂质分子 - 异戊烯醇脂质
• 英文名称: 25-((1S)-10-camphorsulfonyloxy)-27-isopropoxy-26,28-dihydroxycalix[4]arene
• 英文别名: (26,28-dihydroxy-27-propan-2-yloxy-25-pentacyclo[19.3.1.13,7.19,13.115,19]octacosa-1(25),3,5,7(28),9(27),10,12,15(26),16,18,21,23-dodecaenyl) [(1S,4R)-7,7-dimethyl-2-oxo-1-bicyclo[2.2.1]heptanyl]methanesulfonate
• CAS: 1052211-45-6
• 化学式: C₄₁H₄₄O₇S
• 分子量: 680.862
• InChiKey: FPIWWKZZMHQWDG-CZNWIGJESA-N

计算性质

• 辛醇/水分配系数(LogP)：
  8.7
• 重原子数：
  49
• 可旋转键数：
  6
• 环数：
  7.0
• sp3杂化的碳原子比例：
  0.39
• 拓扑面积：
  119
• 氢给体数：
  2
• 氢受体数：
  7

反应信息

• 作为产物：
  描述：

  calix[4]arene monoisopropyl ether 、 右旋樟脑-10-磺酰氯 在 三乙胺 作用下， 以 甲苯 为溶剂， 以85%的产率得到25-((1S)-10-camphorsulfonyloxy)-27-isopropoxy-26,28-dihydroxycalix[4]arene
  参考文献：
  名称：

  Regio- and stereoselective 1(S)-camphorsulfonylation of monoalkoxycalix[4]arenes

  摘要：

  The reaction of calix[4]arene monoalkyl ethers with 1(S)-camphor-10-sulfonyl chloride yields 1,2- or 1,3-alkoxy-1(S)-camphorsulfonyloxycalixarenes depending on the nature of the base used. In the presence of triethylamine only 1,3-substituted derivatives are formed. Two diastereomers of the 1,2-substituted calixarenes with clockwise and anticlockwise arrangement of alkyl and camphorsulfonyl groups at the narrow rim are formed in the presence of sodium hydride or potassium carbonate. Due to chiral induction of the camphorsulfonyl group the 1,2-substitution is diastereoselective. The ratio of diastereomers formed is dependent on the alkyl groups at the calixarene narrow rim. (C) 2008 Published by Elsevier Ltd.

  DOI：

  10.1016/j.tet.2008.05.106

文献信息

• Regio- and stereoselective 1(S)-camphorsulfonylation of monoalkoxycalix[4]arenes
  作者：V.I. Boyko、A.V. Yakovenko、Yu.I. Matvieiev、O.I. Kalchenko、O.V. Shishkin、S.V. Shishkina、V.I. Kalchenko

  DOI：10.1016/j.tet.2008.05.106

  日期：2008.8

  The reaction of calix[4]arene monoalkyl ethers with 1(S)-camphor-10-sulfonyl chloride yields 1,2- or 1,3-alkoxy-1(S)-camphorsulfonyloxycalixarenes depending on the nature of the base used. In the presence of triethylamine only 1,3-substituted derivatives are formed. Two diastereomers of the 1,2-substituted calixarenes with clockwise and anticlockwise arrangement of alkyl and camphorsulfonyl groups at the narrow rim are formed in the presence of sodium hydride or potassium carbonate. Due to chiral induction of the camphorsulfonyl group the 1,2-substitution is diastereoselective. The ratio of diastereomers formed is dependent on the alkyl groups at the calixarene narrow rim. (C) 2008 Published by Elsevier Ltd.